Pro-pigmenting peptides

Abstract

The invention is directed to the use of at least one peptide of formula: X-(Xaa 1 ) n -Pro*-(Xaa 2 ) m -Y (I) With: —n=0, 1 or 2; —m=0 or 1 and if m=0 then n≠0 —Xaa 1 is: —An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; —A polar aminoacid selected from Serine (Ser, S), Threonine (Thr, T), Tyrosine (Tyr, Y), Asparagine (Asn, N), Glutamine (Gln, Q) and analogues and derivatives thereof; —or Glycine (Gly, G); When n=2 the two aminoacids Xaa 1 can be the same or different; —Xaa 2 is: —An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; —A basic aminoacid selected from Arginine (Arg, R), Lysine (Lys, K) and Histidine (His, H) and analogues and derivatives thereof; —Glycine (Gly, G) or Serine (Ser, S); —At the N terminal end of the peptide, X is selected from H, —CO—R 1 and —SO 2 —R 1 ; —At the C terminal end of the peptide, Y is selected from OH, OR 1 , NH 2 , NHR 1 or NR 1 R 2 , R 1 and R 2 being independently from each other, selected from an alkyle, aryle, aralkyle, alkylaryl, alkoxy and aryloxy group, that can be linear, branched, cyclic, poly-cyclic, non-saturated, hydroxylated, carbonylated, phosphorylated and/or sulphured, with the possibility to have in said group skeleton a O, S and/or N heteroatom; —Pro* corresponding to a Proline, an analogue or derivative thereof; Excluding the peptides where X═H and Y═OH, for a non therapeutical cosmetic pro-pigmenting treatment of skin. The invention also encompasses new tripeptides of formula (I) suitable for a non therapeutical cosmetic treatment of skin.

The invention claimed is: 
     
       1. A method of stimulating collagen synthesis in skin of a subject in need thereof comprising topically applying to the skin of said subject at least one peptide selected from the group consisting of X-SPR-Y, X-PPR-Y, X-QPA-Y, X-LPA-Y, X-SPA-Y, X-PM-Y, and X-PA-Y; wherein at the N terminal end of the peptide, X is selected from the group consisting of H, CO—R 1  and —SO 2 -R 1 ; at the C terminal end of the peptide, Y is selected from the group consisting of OH, OR 1 , NH 2 , NHR 1  or NR 1 R 2 ;
 wherein R 1  and R 2  are independent from each other, and selected from the group consisting of an alkyl, aryl, aralkyl, alkylaryl, alkoxy and aryloxy group, and wherein said alkyl, aryl, aralkyl, alkylaryl, alkoxy and aryloxy group can be linear, branched, cyclic, poly-cyclic, non-saturated, hydroxylated, carbonylated, phosphorylated and/or sulfured, and may include an O, S and/or N heteroatom; and 
 wherein the peptide does not include the peptide wherein X═H and Y═OH. 
 
     
     
       2. The method according to  claim 1 , wherein R 1  and/or R 2  are alkyl chains of 1 to 24 carbon atoms. 
     
     
       3. The method according to  claim 2 , wherein R 1  and/or R 2  are alkyl chains of 3 to 24 carbon atoms. 
     
     
       4. The method according to  claim 1 , wherein X is a CO—R 1  acyl group and Y is selected from the group consisting of OH, OMe, OEt and NH 2 . 
     
     
       5. The method according to  claim 4 , wherein Y is OH. 
     
     
       6. The method according to  claim 1 , wherein X is a CO-R 1  acyl group selected from the group consisting of octanoyl (C8), decanoyl (C10), lauroyl (C12), myristoyl (C14), palmitoyl (C16), stearoyl (C18), biotinoyl, elaidoyl, oleoyl and lipoyl. 
     
     
       7. The method according to  claim 6 , wherein X is selected from the group consisting of lauroyl (C12), myristoyl (C14) and palmitoyl (C16). 
     
     
       8. The method according to  claim 1 , wherein said stimulation of collagen synthesis can be used to achieve an anti-aging treatment in the skin of the subject. 
     
     
       9. The method according to  claim 1  wherein said stimulation of collagen synthesis can be used to achieve a volumizing effect in the skin of the subject. 
     
     
       10. The method according to  claim 1 , wherein said stimulation of collagen synthesis can be used to treat wrinkles and fine lines in the skin of the subject.